By a combination of 1D and 2D 1H- and 13C-NMR, FAB-MS, and chemical and enzymatic reactions carried out at the milligram level, it has been demonstrated that syringomycin E, the major phytotoxic antibiotic produced by Pseudomonas syringae pv. syringae, is a new lipodepsipeptide. Its amino acid sequence is Ser-Ser-Dab-Dab-Arg-Phe-Dhb-4(Cl)Thr-3(OH)Asp with the β-carboxy group of the C-terminal residue closing a macrocyclic ring on the OH group of the N-terminal Ser, which in turn is N-acylated by 3-hydroxydodecanoic acid. Syringomycins A1 and G, two other metabolites of the same bacterium, differ from syringomycin E only in their fatty acid moieties corresponding, respectively, to 3-hydroxydecanoic and 3-hydroxytetradecanoic acid
The structure of syringomycins A1, E and G / A., Segre; R. C., Bachmann; Ballio, Alessandro; Bossa, Francesco; Grgurina, Ingeborg; N. S., Iacobellis; G., Marino; P., Pucci; Simmaco, Maurizio; J. Y., Takemoto. - In: FEBS LETTERS. - ISSN 0014-5793. - STAMPA. - 255:(1989), pp. 27-31. [10.1016/0014-5793(89)81054-3]
The structure of syringomycins A1, E and G
BALLIO, Alessandro;BOSSA, Francesco;GRGURINA, Ingeborg;SIMMACO, Maurizio;
1989
Abstract
By a combination of 1D and 2D 1H- and 13C-NMR, FAB-MS, and chemical and enzymatic reactions carried out at the milligram level, it has been demonstrated that syringomycin E, the major phytotoxic antibiotic produced by Pseudomonas syringae pv. syringae, is a new lipodepsipeptide. Its amino acid sequence is Ser-Ser-Dab-Dab-Arg-Phe-Dhb-4(Cl)Thr-3(OH)Asp with the β-carboxy group of the C-terminal residue closing a macrocyclic ring on the OH group of the N-terminal Ser, which in turn is N-acylated by 3-hydroxydodecanoic acid. Syringomycins A1 and G, two other metabolites of the same bacterium, differ from syringomycin E only in their fatty acid moieties corresponding, respectively, to 3-hydroxydecanoic and 3-hydroxytetradecanoic acidI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
